Hair treatment composition and methods

Abstract

wherein D is a chromophore; L is a linking group selected from SO 2 , NHCO, and NHSO 2 ; Q is a hydrogen or halogen atom; and R is selected from C 1 -C 4 alkyl, (CH 2 ) n COOH, (CH 2 ) n CONH 2 , (CH 2 ) n SO 3 H, (CH 2 ) n COOM, (CH 2 ) n PO 3 H, (CH 2 ) n OH, (CH 2 ) n SSO 3 ″, (CH 2 ) n NR 1 2 , (CH 2 ) n N + R 1 H 2 , (CH 2 ) n NHCOR 1 , PhSSO 3 ″, PhSO 3 H, PhPO 3 H, PhNR 1 2 , PhN + R 1 3 , (CH 2 ) 2 CH(SH)R 1 (CH 2 ) 3 COOH, and n is an integer in the range of 1 to 4 wherein within the same molecule each n is not necessarily the same integer; M is a cation of an alkaline earth metal, alkali metal, NH4+ or NR 1 3 + ; and R 1 is C 1 -C 4 alkyl.

1. A compound of formula (I)
   D-L-CHQ-CH 2 —SR  (I)
 
 
       wherein D is a chromophore; L is a linking group selected from SO 2 , NHCO, and NHSO 2 ; Q is a hydrogen or halogen atom; and R is selected from C 1 -C 4  alkyl, (CH 2 ) n COOH, (CH 2 ) n CONH 2 , (CH 2 ) n SO 3 H, (CH 2 ) n COOM, (CH 2 ) n PO 3 H, (CH 2 ) n OH, (CH 2 ) n SSO 3   − , (CH 2 ) n NR 1   2 , (CH 2 ) n N + R 1 H 2 , (CH 2 ) n NHCOR 1 , PhSSO 3   − , PhSO 3 H, PhPO 3 H, PhNR 1   2 , PhN + R 1   3 , (CH 2 ) 2 CH(SH)R 1 (CH 2 ) 3 COOH, and 
       
         
           
           
               
               
           
         
       
       n is an integer in the range of 1 to 4 wherein within the same molecule each n is not necessarily the same integer; M is a cation of an alkaline earth metal, alkali metal, NH 4   +  or NR 1   3   + ; and R 1  is C 1 -C 4  alkyl. 
     
     
       2. A compound according to  claim 1  wherein Q is hydrogen. 
     
     
       3. A compound according to  claim 1  wherein L is SO 2 . 
     
     
       4. A compound according to  claim 1  wherein the group SR in formula (I) is SCHR 2 R 3 ; wherein R 2  is selected from (CH 2 ) m COOX, (CH 2 ) m SO 3 X, (CH 2 ) m NH 2 , (CH 2 ) m NR 4 R 5 , (CH 2 ) m NHCOR 4  and (CH 2 ) m CH(COOX)NH 2 ; wherein m is an integer of from 0 to 3, and X is selected from hydrogen, an alkali metal, a C 1  to C 4  alkyl group and a substituted or unsubstituted ammonium salt; R 4  is a C 1  to C 4  alkyl group and R 5  is selected from hydrogen and a C 1  to C 4  alkyl group; and R 3  is selected from hydrogen, an alkyl group having 1 to 4 carbon atoms, an ester, an acid, an amide, an amine residue or an alcohol residue. 
     
     
       5. A compound according to  claim 1  having the structure of formula (III) or formula (IV):
   D-SO 2 —CH 2 —CH 2 —SCH 2 COOH  (III)
 
   D-SO 2 —CH 2 —CH 2 —SCH 2 CH(COOH)NH 2   (IV)
 
 
       or an ester or salt thereof. 
     
     
       6. A method of preparing a compound as claimed  claim 1 , the method comprising reacting a compound of formula (X) or (X′) with a thiol of formula (XI): 
       
         
           
           
               
               
           
         
       
       wherein R, D and L are as defined in  claim 1  and Y is a leaving group. 
     
     
       7. A composition for colouring a material comprising a compound as claimed in  claim 1  and a diluent or carrier. 
     
     
       8. A composition according to  claim 7  wherein the compounds of  claim 1  are formed in situ. 
     
     
       9. A composition according to  claim 7  which further comprises a thiol selected from thioglycolic acid, thiolactic acid, dihydrolipoate, thioglycerol, mercaptopropionic acid, cysteine, N-substituted cysteines, cysteamines, N-substituted cysteamines, thioethanol and 1-thiopropane 3-sulfonate. 
     
     
       10. A composition according to  claim 7  which further comprises urea. 
     
     
       11. A method of dyeing fibres, the method comprising applying to the fibres a composition as claimed in  claim 7 . 
     
     
       12. A hair treatment method comprising the steps of:
 (a) optionally bleaching the hair; 
 (b) dyeing the hair by applying a composition as claimed in  claim 7 ; and 
 (c) optionally removing colour from the hair by applying a colour removal composition comprising a sulfur-containing nucleophile.